Octanedioic acid bis-[(3S,10R,13R,17R)-17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] ester | 38698-81-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: Octanedioic acid bis-[(3S,10R,13R,17R)-17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] ester
• 英文别名: 1,8-octanedicarboxylic acid dicholesteryl ester；dicholesteryl suberate；Korksaeure-dicholesterylester；Dicholesteryl-suberat
• CAS: 38698-81-6
• 化学式: C₆₂H₁₀₂O₄
• 分子量: 911.489
• InChiKey: BGKMPKSPDQBWLZ-ZMSPHZEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.23
• 重原子数：
  66.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  胆固醇 、 1,8-二辛酰氯 以 甲苯 为溶剂， 反应 3.0h， 以80%的产率得到Octanedioic acid bis-[(3S,10R,13R,17R)-17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] ester
  参考文献：
  名称：

  Thermal and optical properties of chiral twin liquid crystalline bis(cholesteryl) alkanedioates

  摘要：

  The thermal and optical properties of a series of bis (cholesteryl) alkanedioates were investigated. The melting points, the cholesteric to isotropic transition temperatures, the entropy changes at this temperature and the selective reflection wavelengths of the cholesteric phase all exhibit an odd-even effect as a function of spacer length. This is attributed to a difference in the ordering of the cholesteric phase as a function of the parity of the spacer. Because the properties of the members of the series with a short spacer could not be measured for several reasons, their properties were also determined as a 5 wt% solution in a cholesteric host. A similar odd-even influence on the cholesteric to isotropic transition temperatures and the optical properties of the host was observed as for the pure compounds. The influence on the properties of the host is stronger for compounds with a short spacer than for compounds with a longer spacer.

  DOI：

  10.1039/jm9960601469

文献信息

• Steryl and Stanyl Esters of Fatty Acids by Solvent-Free Esterification and Transesterification in Vacuo Using Lipases from <i>Rhizomucor miehei</i>, <i>Candida antarctica</i>, and <i>Carica papaya</i>
  作者：Nikolaus Weber、Petra Weitkamp、Kumar D. Mukherjee

  DOI：10.1021/jf0107407

  日期：2001.11.1

  Sitostanol has been converted in high to near-quantitative extent to the corresponding long-chain acyl esters via esterification with oleic acid or transesterification with methyl oleate or trioleoylglycerol using immobilized lipases from Rhizomucor miehei (Lipozyme IM) and Candida antarctica (lipase B, Novozym 435) as biocatalysts in vacuo (20-40 mbar) at 80 degreesC, whereas the conversion was markedly lower at 60 and 40 degreesC. Corresponding conversions observed with papaya (Carica papaya) latex lipase were generally lower. High conversion rates, observed in transesterification of sitostanol with methyl oleate at 80 degreesC using Lipozyme IM were retained even after 10 repeated uses of the biocatalyst. Saturated sterols such as sitostanol and 5 alpha -cholestan-3 beta -ol were the preferred substrates as compared to Delta (5)-unsaturated cholesterol in transesterification reactions with methyl oleate using Lipozyme IM. Transesterification of cholesterol with dimethyl 1,8-octanedioate using Lipozyme IM in vacuo yielded methylcholesteryl 1,8-octanedioate (75%) and dicholesteryl 1,8-octanedioate (5%). However, transesterification. of cholesterol with diethyl carbonate and that of oleyl alcohol with ethylcholesteryl carbonate, both catalyzed by Lipozyme IM, gave ethylcholesteryl carbonate and oleylcholesteryl carbonate, respectively, in low yield (20%). Moreover, cholesterol was transesterified with ethyl dihydrocinnamate using Lipozyme IM to give cholesteryl dihydro cinnamate in moderate yield (56%), whereas the corresponding reaction of lanosterol gave lanosteryl oleate in low yield (14%).
• Page; Rudy, Biochemische Zeitschrift, 1930, vol. 220, p. 304,308, 321
  作者：Page、Rudy

  DOI：——

  日期：——